4"-N-(Substituted)-apramycin antibiotic derivatives and intermediates therefor

Abstract

Apramycin derivatives substituted at the 4"-amino group with a variety of substituents are broad spectrum antibiotics. Also claimed are intermediates in the synthesis of these apramycin derivatives.

I claim: 
     
       1. A compound of the formula ##STR8## wherein R 1  is C 2  to C 4  -alkyl, C 1  to C 4  -acyl, benzyl, methoxybenzyl, halobenzyl, γ-amino-α-hydroxybutyryl, β-amino-α-hydroxypropionyl, glycyl, 4-amino-2-hydroxybutyl, 3-amino-2-hydroxypropyl or 2-aminoetyl; and the pharmaceutically acceptable acid addition salts thereof. 
     
     
       2. A compound of claim 1, wherein R 1  is C 2  to C 4  -alkyl. 
     
     
       3. The compound of claim 2, wherein R 1  is ethyl. 
     
     
       4. The compound of claim 1, wherein R 1  is benzyl. 
     
     
       5. A compound of claim 1, wherein R 1  is C 1  to C 4  -acyl. 
     
     
       6. The compound of claim 5, wherein R 1  is acetyl. 
     
     
       7. The compound of claim 1, wherein R 1  is γ-amino-α-hydroxybutyryl. 
     
     
       8. A compound of the formula ##STR9## wherein R 2  is C 1  to C 4  -acyl, γ-phthalimido-α-hydroxybutyryl, β-phthalimido-α-hydroxypropionyl or N-phthalimidoglycyl; R 3  is benzyloxycarbonyl and   R 4  and R 4  ' are each methyl, or, taken together form a cyclohexyl ring.   
     
     
       9. A compound of claim 8, wherein R 2  is γ-phthalimido-α-hydroxybutyryl. 
     
     
       10. The compound of claim 9, wherein R 4  and R 4  ' are each methyl. 
     
     
       11. A compound of the formula ##STR10## wherein R 5  is C 1  -C 4  -acyl, γ-phthaliido-α-hydroxybutyryl, β-phthalimido-α-hydrxypropionyl or N-phthalimidoglycyl; and R 6  is benzyloxycarbonyl. 
     
     
       12. The compound of claim 11, wherein R 5  is γ-phthalimido-α-hydroxybutyryl. 
     
     
       13. A compound of the formula ##STR11## wherein R 7  is γ-phthalimido-α-hydroxybutyryl, β-phthalimido-α-hydroxypropionyl or N-phthalimidoglycyl. 
     
     
       14. The compound of claim 13, wherein R 7  is γ-phthalimido-α-hydroxybutyryl.